A variety of 1,2-dioxetane derivatives have so far been synthesized, and it is known that compounds having a spiroadamantyl group in the 3-position are particularly useful chemiluminescent materials (e.g. Japanese Kokai Publication Hei-5-21918 and Japanese Kokai Publication Hei-5-45590).
Furthermore, as compounds synthesized by the present inventors, the compounds disclosed in Japanese Kokai Publications Hei-8-245615, Hei-8-169885, and Hei-8-165287 are known. However, those 1,2-dioxetane derivatives do not have good thermal stability. The Japanese Kokai Publication Hei-9-216887 referred to above discloses a compound with improved thermal stability.
In regard of such 1,2-dioxetane derivatives, much research has been undertaken as inferable from the above list of publications and new compounds have also been created. Therefore, it is necessary for applying to a clinical examination and other fields to have a substance with a good thermal stability, easiness of handling, and high in emission efficiency.
However, those known compounds, e.g. compounds described in Japanese Kokai Publication Hei-9-216887 have the drawback that their chemiluminescent emission efficiencies are considerably sacrificed in the presence of protic solvents. Therefore, when used in immunoassays in a clinical examination, for instance, those compounds failed to give a practically useful intensity of emission when the assay system includes a protic solvent. Therefore, it is necessary to have a substance capable of increasing the intensity of emission, the so-called enhancer, to coexist in the system. Therefore, a compound showing high emission efficiency without coexisting enhancer in the system even in a protic solvent is more available.
Furthermore, in a clinical examination performed using an automatic instrument, for instance, compounds differing in emission wavelength from the conventional chemiluminescent materials should be of great use, for the detection and determination of a plurality of test items can be simultaneously performed. Moreover, if the difference in color be of the order which can be visually detected, such compounds should be of great convenience and are expected to find application in a variety of uses.